242 Windward Dr, Osprey, FL 34229
OFF MARKET

$964,700

Trulia Estimate
  • 4 Beds
  • 3 Baths
  • 2,986 sqft (on 0.30 acres)

242 Windward Dr, Osprey, FL 34229

Est. Refi. Payment $6,056/mo*
Refinance Your Home
Currently Off Market - Sold May 31, 2013 for $515,000

Home Value

Trulia Estimate
$965K
Since last month
Increased$17K (+1.8%)
Since last year
Increased$9K (+0.9%)
Since last sale
Increased$452K (+87.8%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +58% in the last 10 years
MonthEstimated value
2026
August 2026$967K
August 2026$965K
July 2026$950K
June 2026$991K
May 2026$957K
April 2026$990K
March 2026$959K
February 2026$970K
January 2026$956K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
216 WINDWARD DRIVE, Osprey, FL
0.04
Single-Family Home
$600,000
11/18/25
3
3
2,575
204 WINDWARD DRIVE, Osprey, FL
0.06
Single-Family Home
$800,000
08/24/26
3
3
2,486
186 WINDWARD DRIVE, Osprey, FL
0.09
Single-Family Home
$565,000
07/20/26
3
2
2,505
1218 YACHT HARBOR DRIVE, Osprey, FL
0.06
Single-Family Home
$1,025,000
04/24/26
3
3
3,297
1235 YACHT HARBOR DRIVE, Osprey, FL
0.07
Single-Family Home
$1,065,000
02/20/26
3
3
2,698
447 OAK POINT ROAD, Osprey, FL
0.18
Single-Family Home
$520,000
12/30/25
4
3
2,688
102 WINDWARD DRIVE, Osprey, FL
0.22
Single-Family Home
$565,000
06/04/26
3
2.5
2,134
114 Windward Dr, Osprey, FL
0.20
Single-Family Home
$585,000
06/02/26
3
2
2,037
264 WOODS POINT ROAD, Osprey, FL
0.16
Single-Family Home
$425,000
10/29/25
2
3
2,837
486 YACHT HARBOR DRIVE, Osprey, FL
0.15
Single-Family Home
$1,325,000
08/25/26
3
3.5
2,939

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
1218 YACHT HARBOR DRIVE, Osprey, FL 34229
0.06
$1,025,000
3
3
3,297
Recently Sold
1235 YACHT HARBOR DRIVE, Osprey, FL 34229
0.07
$1,065,000
3
3
2,698
Recently Sold
216 WINDWARD DRIVE, Osprey, FL 34229
0.04
$600,000
3
3
2,575
Recently Sold
1237 FLYING BRIDGE LANE, Osprey, FL 34229
0.09
$842,800
3
2
2,045
Off Market
204 WINDWARD DRIVE, Osprey, FL 34229
0.06
$800,000
3
3
2,486
Recently Sold
186 WINDWARD DRIVE, Osprey, FL 34229
0.09
$565,000
3
2
2,505
Recently Sold
486 YACHT HARBOR DRIVE, Osprey, FL 34229
0.15
$1,325,000
3
3.5
2,939
Recently Sold
188 DORY LANE, Osprey, FL 34229
0.12
$787,700
3
2
2,069
Off Market
1140 BEACHCOMBER COURT #11, Osprey, FL 34229
0.13
$540,000
3
2.5
2,040
For Sale
1110 BEACHCOMBER COURT #1, Osprey, FL 34229
0.13
$461,200
3
2.5
2,166
Off Market
1116 BEACHCOMBER COURT #3, Osprey, FL 34229
0.13
$530,000
3
2.5
2,040
Recently Sold
1164 BEACHCOMBER COURT #19, Osprey, FL 34229
0.13
$519,300
3
2.5
1,952
Off Market

Local Information

  • Map ViewExplore the area around 242 Windward Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 2001
0.3 acre lot
2,986 sqft
$323/sqft
Garage

About this House

Newer than the rest with all the bells and whistles/Immaculately maintained/Granite/High ceilings/Art glass accents/Custom-built closets/2 1/2 car garage/Enormous laundry room/Central vac/Crown molding/Alarm/Fruit trees/Deep water marina for use by Southbay residents only, 50' community heated pool, tennis courts, 20 acres of parks with 5 miles of jogging paths and MORE ! Brokered And Advertised By: BILLIB & BILLIB P A Listing Agent: DEREK BILLIB
242 Windward Dr, Osprey, FL 34229 is a 4 bedroom, 3 bathroom, 2,986 sqft single-family home built in 2001. It last sold for $515,000 on May 31, 2013. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $964,700, with a rent estimate of $4,405/month.

Home Details for 242 Windward Dr

Interior Features

Levels, Entrance, & Accessibility
Stories: 1Floors: Carpet
Interior Details
Number of Rooms: 7
Heating & Cooling
Air Conditioning

Exterior Features

Exterior Home Features
Roof: OtherExterior: StuccoFoundation Type: ConcretePatio
Pool
Pool
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 2001Year Updated: 2001
Property Type / Style
Property Type: Single Family Home

Rental Terms, Policies & Fees

Furnished

Community

Units in Building: 1

Lot Information

Lot Area: 0.30 acres

Building

Fitness & Sports
Tennis Court

Price and Tax history

DateEventPrice
May 31, 2013
Source: N/A
Sold
$515,000
Mar 9, 2013
Source: Agent Provided
PriceChange
$574,000
Price decreased by 4%
Sep 6, 2012
Source: Agent Provided
Listed For Sale
$599,000
May 13, 2012
Source: Agent Provided
ListingRemoved
$574,000
May 3, 2012
Source: Agent Provided
Listed For Sale
$574,000

Market trends in Osprey

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
133
7MoM

Around this home

What Locals Say about Osprey

At least 46 Trulia users voted on each feature.

  • 90 % Say car is needed

  • 87 % Say it's dog friendly

  • 85 % Say it's quiet

  • 84 % Say parking is easy

  • 75 % Say people would walk alone at night

  • 74 % Say there's wildlife

  • 67 % Say yards are well-kept

  • 67 % Say there's holiday spirit

  • 64 % Say they plan to stay for at least 5 years

  • 54 % Say neighbors are friendly

  • 48 % Say there are sidewalks

  • 42 % Say it's walkable to restaurants

  • 42 % Say streets are well-lit

  • 41 % Say it's walkable to grocery stores

  • 41 % Say there are community events

  • 31 % Say kids play outside

Sourced by Trulia users. Learn more about our methodology.
  • Lindsey W.
    "It’s a quiet and low key suburb area of Sarasota county. It’s very accessible to I-75 and Nokomis beach and about a 25 minute drive to siesta key beach. "
    4
    Flag
  • Mary V.
    "I am retired now but my commute to Stickney Point was only about 10 min and downtown was about 25 min during rush hour when there is no construction "
    0
    Flag
  • Mary V.
    "Pineview School is very close, nice safe area for children. CVS and Publix are also close, as well as Historic Spanish Pointe. The beach is ten minutes or less."
    3
    Flag
  • Bob T.
    "I don’t commute....retired. There are no sidewalks here and our street has a large amount of speeders making walking dangerous. Some neighbors park on the county right of way destroying our water flow/drainage which has caused flooding here. Many homes are unkept even though there is an active hoa."
    14
    Flag
  • Bob T.
    "Neighborhood is pet friendly. Wide road we walking dogs. Only problem noticed now is daily construction vehicles speeding in neighborhood."
    1
    Flag
  • Larysathor
    "Well, the Mother Nature taking its tall, water level raised over last ten years and a lot of beaches are washed out to nonexistence."
    0
    Flag
  • Brenda F. D.
    "Neighborhood is beautiful love the area close to everything and beaches and shopping . Local restaurant "
    1
    Flag
  • Michelle C.
    "I've lived in this neighborhood for twenty years +. My neighbors are the friendliest. We all look out for each other and lend a hand when needed. Can't think of anywhere else I'd want to live."
    0
    Flag
  • nancybuscher
    "This quiet, beautifully landscaped, pet friendly subdivision is close to beaches, shopping, restaurants, cultural events in Sarasota and Venice, beside Oscar Scherer State Park for hickers & boaters, and has easy access to airports by way of US41 & I-75."
    0
    Flag
  • info
    "Centrally located, minutes to beaches and shopping"
    1
    Flag
  • bookwoman39
    "Wonderful community, close to Sarasota and all restaurants, cultural activities, etc. The condo development is a designated bird sanctuary. Nice pools, exercise room, community room. Good neighbors. What the development lacks is diversity. "
    0
    Flag
  • trishmainey1111
    "Osprey Florida is one of the most beautiful, accessible communities in Florida. Ten minutes to the white sands beach and ten minutes to I-75. "
    1
    Flag
  • Gail L.
    "I work here, belong to the club and have lived in the neighborhood for the last 12 years it is one of 5 golf communities I have belonged to and bar none my favorite due to the people that live here. They are multicultural, down to earth and just fabulous. This is a community that rates above the rest . it is very common for folks to move up and down in house sizes and styles as their lifestyles change. Give me a call as I'd love to show you around. "
    0
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 242 Windward Dr

  • What is 242 Windward Dr estimated to be worth?
    Trulia's estimated value for 242 Windward Dr in Osprey, FL is $964,700.
  • What is the price history for 242 Windward Dr?
    242 Windward Dr in Osprey, FL last sold for $515,000 in May 2013.
  • Is Osprey a buyer's or seller's market?
    Osprey is currently a buyer's market, based on recent for-sale activity.
  • What do residents say about Osprey?
    Residents describe Osprey, FL as dog-friendly, quiet, and easy to park in. Most residents say you need a car. See recently sold homes in Osprey, FL.
  • Does 242 Windward Dr have a pool?
    Yes, 242 Windward Dr in Osprey, FL has a pool.
  • How big is the lot at 242 Windward Dr?
    The lot at 242 Windward Dr in Osprey, FL is about 0.30 acres (13,068 sq ft).

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